Pharmaceutical compounds

Abstract

Therapeutically-effective amounts of novel analogs or derivatives of alkyl fatty acids, such as but not limited to lipoic acid, and pharmaceutical formulations comprising such analogs or derivatives and pharmaceutically-acceptable carriers therefor, are useful for the treatment, prevention, imaging, and/or diagnosis of medical disorders.

The invention to be claimed is: 
     
       1. An alkyl fatty acid analog having the general formula: 
       
         
           
           
               
               
           
         
       
       wherein:
 n is 2; 
 x is 1-16; 
 R 1  and R 2  are independently alkylaryl or alkylheteroaryl; and 
 R 5  is heteroaryl attached to the (CH n ) x  via a carbon atom of the heteroaryl group; 
 or a salt thereof. 
 
     
     
       2. The analog of  claim 1 , wherein R 1  and R 2  are independently alkylaryl. 
     
     
       3. The analog of  claim 1 , wherein R 1  and R 2  are independently alkylheteroaryl. 
     
     
       4. The analog of  claim 1 , wherein the heteroaryl is a 5-membered or 6-membered monocyclic aromatic ring containing 1-4 heteroatoms selected from the group consisting of S, N, and O. 
     
     
       5. The analog of  claim 2 , wherein the heteroaryl is a 5-membered or 6-membered monocyclic aromatic ring containing 1-4 heteroatoms selected from the group consisting of S, N, and O. 
     
     
       6. The analog of  claim 1 , wherein the heteroaryl is unsubstituted. 
     
     
       7. The analog of  claim 4 , wherein the heteroaryl is unsubstituted. 
     
     
       8. The analog of  claim 5 , wherein the heteroaryl is unsubstituted. 
     
     
       9. The analog of  claim 1 , wherein the heteroaryl is substituted by one or more substituents independently selected from the group consisting of alkyl, alkenyl, alkynyl, acyl, alkoxycarbonyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, cyano, halogen, hydroxy, nitro, trifluoromethyl, trifluoromethoxy, trifluoropropyl, amino, amido, alkylamino, dialkylamino, dialkylaminoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthio, —SO 3 H, —SO 2 NH 2 , —SO 2 NH(alkyl), —SO 2 N(alkyl) 2 , —CO 2 H, —CO 2 NH 2 , —CO 2 NH(alkyl), and —CO 2 N(alkyl) 2 . 
     
     
       10. The analog of  claim 4 , wherein the heteroaryl is substituted by one or more substituents independently selected from the group consisting of alkyl, alkenyl, alkynyl, acyl, alkoxycarbonyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, cyano, halogen, hydroxy, nitro, trifluoromethyl, trifluoromethoxy, trifluoropropyl, amino, amido, alkylamino, dialkylamino, dialkylaminoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthio, —SO 3 H, —SO 2 NH 2 , —SO 2 NH(alkyl), —SO 2 N(alkyl) 2 , —CO 2 H, —CO 2 NH 2 , —CO 2 NH(alkyl), and —CO 2 N(alkyl) 2 . 
     
     
       11. The analog of  claim 5 , wherein the heteroaryl is substituted by one or more substituents independently selected from the group consisting of alkyl, alkenyl, alkynyl, acyl, alkoxycarbonyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, cyano, halogen, hydroxy, nitro, trifluoromethyl, trifluoromethoxy, trifluoropropyl, amino, amido, alkylamino, dialkylamino, dialkylaminoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthio, —SO 3 H, —SO 2 NH 2 , —SO 2 NH(alkyl), —SO 2 N(alkyl) 2 , —CO 2 H, —CO 2 NH 2 , —CO 2 NH(alkyl), and —CO 2 N(alkyl) 2 . 
     
     
       12. A pharmaceutical formulation comprising at least one alkyl fatty acid analog of  claim 1  and at least one pharmaceutically acceptable carrier. 
     
     
       13. A pharmaceutical formulation comprising at least one alkyl fatty acid analog of  claim 4  and at least one pharmaceutically acceptable carrier. 
     
     
       14. A pharmaceutical formulation comprising at least one alkyl fatty acid analog of  claim 5  and at least one pharmaceutically acceptable carrier. 
     
     
       15. A method of treating a disease selected from primary melanoma, metastatic melanoma, lung cancer, liver cancer, Hodgkin's lymphoma, non-Hodgkin's lymphoma, uterine cancer, cervical cancer, bladder cancer, kidney cancer, colon cancer, breast cancer, prostate cancer, ovarian cancer, pancreatic cancer, and a sarcoma, comprising administering to a patient in need thereof a therapeutically effective amount of at least one alkyl fatty acid analog according to  claim 1  to treat the disease. 
     
     
       16. The method of  claim 15 , wherein the disease is lung cancer, pancreatic cancer, or a sarcoma. 
     
     
       17. The method of  claim 15 , wherein the at least one alkyl fatty acid analog is the analog according to  claim 4 . 
     
     
       18. The method of  claim 15 , wherein the at least one alkyl fatty acid analog is the analog according to  claim 5 .